Autumn Headwear

hat headwear for fall

Fall/Winter is coming and I could not be happier.  It’s a time where we can take advantage of the weather and wear what makes classic menswear enjoyable, like textures and layers. I’ve already been in a cold weather mood with my brown checked jackets, but there’s another old friend I’ve been wanting to welcome back, perhaps as a way to cheer me up from how 2020 has been going: hats.

Obviously, hats are nothing new in menswear; once upon a time, men were seldom seen out of the house without a fedora. Unfortunately, that time has long passed due to JFK or closed roof automobiles (depending on your source).  However, the demise of the fedora hasn’t stopped men from wearing them and we can’t deny their practicality, especially in the colder months.  

Hats are so much more than just practical head coverings; each one has a distinct vibe that can either play into or subvert your overall outfit. It definitely is something to consider today, as the Quarantine World has popularized relaxed dress codes, allowing for a greater variance with menswear attire. No longer do you have to worry about being too casual or being delightfully contrarian; we’re finally starting to be able to dress the way we want to, and that includes incorporating “unorthodox” hats,” hat hair” be damned. 


Caps, whether the words “dad” or “ball” precede them, are probably one of the easiest to get into.  A carry-over from skate and prep style, the cap has certainly been making inroads in the classic menswear community.  There’s just something inherently slouchy and easy about a cap: it comes off as if you simply grabbed it on your way out the door.  Sure, it may not “go” with a worsted business suit, but I think it’s perfectly fine with a navy blazer and grey trousers.
As it’s getting colder, I think the casual cap plays perfectly with tweed jacketing and flannel trousers; a denim or chambray shirt signifies you’re dressing for fun rather than work. In a world where we don’t have to dress up, including a cap into an outfit leans into my mantra that I’m just wearing clothes I like- they just happen to be tailored.

Plenty of brands have been diving deep into the cap trend lately, with the most prominent one being Rowing Blazers. Others have followed suit, like Drake’s with their racquet club needlecord caps a few seasons ago or the Wm Brown trucker. I’m sure you could find plenty of brands that make a good cap, whether you want something refined from Loro Piana or something a bit novel made from corduroy or with fun embroidery on the front.

Personally, I like caps that have a personal connection to the wearer.  They make it just a bit more fun and make its inclusion in a menswear outfit feels natural rather than simply taking part in a trend (and there’s nothing wrong with that). I like a hat that displays “What’s Funny” embroidered boldly on the front- it’s an inside joke between my friends and keen listeners of my podcast.  I’ve also worn a VAN JAC cap (purchased during a trip to Tokyo) and a thrifted piece that has “The Fugitive” emblazoned on it; I’m still unsure if the latter was merch or production swag.  My friends have since started to find quirky hats that make sense to them, whether it’s a hat from their alma mater or simply something from Rowing Blazers that features their town.

Knit caps/Berets

Knit caps (or beanies) are the next step “up” from the cap.  In terms of utility, it outclasses the cap, at least when warmth is concerned.  Obviously, it’s even more casual than the cap, since it provides no “shape”, but I think that’s what makes the knit cap a great choice for headwear.  If the key to the ball cap is to embrace the youthful, ivy-student vibe, then the beanie allows a wearer to embrace a rugged, workwear-esque appearance.

A chore coat, peacoat, or even an overcoat feels right at home for a beanie, so don’t worry about its versatility. When I do it, I actually prefer a beanie over a brimmed dad cap. It just feels easier to wear and less fussy, as you don’t have to worry about logos. Grab a navy one or add in character with bold colors or a fun donegal.  I don’t think I even have to bring up Steve Zizzou to remind you that vibrant colors are also a great choice to be a bit quirky.

If you want a more refined hat that is similar to the beanie, then I recommend the beret. With its traditional black color and eccentric stem, the beret has European/intellectual allure that provides an edgier spin on sartorial headwear. While I certainly got inspired by Ethan Newton and Kenji over at Brycelands, I’ve seen it pop up more often, especially by a few Japanese menswear brands as well as on the boys over at The Anthology Taiwan.

The beret might seem intimidating at first, but really is just an extension of the knit cap.  Instead of hugging your head, it usually has some slack to it, allowing the wearer to mess with it as needed to provide the perfect amount of slouch.  I find that it really adds an extra layer of interest to an outfit, whether I’m wearing a tie or not.  Plus, it definitely keeps your head warm.  I recommend looking on eBay for vintage ones (I’d avoid military ones), but I think that H.W Dog and Co are worth a look; they even made an open weave one that is perfect for LA, as it never gets too cold here in Southern California.

Bucket Hats

Bucket hats have also been seeing a resurgence, most likely on the tail end of the dad cap thanks to the growing influence of street/skate wear in classic menswear. This hat can also skew a bit preppy, as the classic khaki model with the iconic red/blue band, is probably the most ivy-prep you could be. As a result, it works well with all types of “casual” tailoring, from cotton twill suits to tweed jackets and hearty oxfords. It’s also the most practical, as its full brim can protect you from the elements while the entire hat can be “crushed” and packed away as needed. 

After the beret, the bucket hat might be my absolute favorite headwear all year-round. I obtained mine from the Put This On Shop a few years ago and it’s been lovingly worn everywhere, from a summer trip to Japan to LA during rainy days. In keeping with the theme, the bucket hat definitely subverts a lot of my classic attire while also making some dressed-down outfits a bit more interesting.  In my mind, it’s a bit like rekindling my days as a toddler in the 90s, just with custom tailoring.


Lastly, we have the fedora.  Now, I know that this is going to take some selling, but hey, I’ve already written about it for the Journal before, so I hope you’ve opened your mind a little bit since then. Full brimmed, felt hats (beaver is best over wool) are incredibly uncommon due to their vintage connotations. However, that’s exactly why I think you should consider them. 

I’ve really come around to wearing my bespoke Wellema fedoras (one brown, one black) much more often lately.  With the lax dress codes, it adds a bit of pizzazz, making an outfit a bit more special and interesting to me. I try not to wear it with a full suit and tie too often, instead opting to wear it with open collar shirts, textured sportshirts, and chinos/denims. However, there are times when I can’t resist the temptation of going full dandy, though my interpretation may be considerably more conservative than I was in my youth. 

I personally believe that a fedora, as well as all the other hats mentioned here, get easier to pair the more you wear them. Not only will you gain confidence, but the hats will break in over the course of the fall/winter and gain character like your favorite pair of jeans. Then, when you do decide to wear it with tailoring, it will feel like a trusty friend, ready to keep you warm and protected from the elements.

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Ethan Wong lives right in the middle: he’s too modern for the vintage scene and yet too vintage for classic menswear. When not at work, he spends his time writing and taking pictures for his blog, Street x Sprezza, which is all about bringing vintage style into the modern day. With a large collection of thrifted vintage and contemporary clothing, he often wonders when his closet will finally implode.

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About Ethan Wong

Ethan Wong lives right in the middle: he’s too modern for the vintage scene and yet too vintage for classic menswear. When not at work, he spends his time writing and taking pictures for his blog, Street x Sprezza, which is all about bringing vintage style into the modern day. With a large collection of thrifted vintage and contemporary clothing, he often wonders when his closet will finally implode.

4 thoughts on “Autumn Headwear

  1. Ethan, You make any hat look good. That is especially true of berets. You’ve inspired me.
    Where do you think a chauffeur’s or news boy’s cap fits in? While a beret feels like a stretch, a chauffeur’s seems less so.
    Your thoughts are always appreciated.

    • Hey Rich!

      Glad to provide some inspiration! It’s funny, I think that news boy caps are a stretch to me due to Dapper Day/Peaky Blinder connotations. The beret feels delightfully “indie”, but that could be just my personality.

      I think plenty of guys rock the newsboy cap though! He Spoke Style, Erik Mannby, Ethan Newton, Mark Cho and so on. Getting it in a tweed or even a chambray is a good way to lean into the rugged vibe and wear with textured suits or even casual attire.

  2. I allways have avoided hats because my head is oversized! so hat makes my head look even bigger, and also almost noone makes hats in my size.. and going bespoke just to see if it will grow on me feels a bit foolish.

  3. No mention of flat caps , beloved of sporting English country gentlemen and East End ‘barrow boys’.

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